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Merck

SML0406

Sigma-Aldrich

Roquefortine C

≥98% (HPLC), from Penicillium roqueforti

Sinónimos:

2H-Pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione, 10b-(1,1-dimethyl-2-propen-1-yl)-6,10b,11,11a-tetrahydro-3-(1H-imidazol-5-ylmethylene)-,(3E,5aS,10bR,11aS)-, Roquefortine from Penicillium roqueforti

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About This Item

Fórmula empírica (notación de Hill):
C22H23N5O2
Número de CAS:
Peso molecular:
389.45
Código UNSPSC:
12161501
NACRES:
NA.77

origen biológico

Penicillium roqueforti

Nivel de calidad

Ensayo

≥98% (HPLC)

solubilidad

chloroform: 1 mg/mL
ethyl acetate: 1 mg/mL
DMSO: 10 mg/mL
methanol: 10 mg/mL

temp. de almacenamiento

−20°C

cadena SMILES

N21C3Nc4c(cccc4)C3(CC2C(=O)N\C(=C/c5nc[nH]c5)\C1=O)C(C)(C)C=C

InChI

1S/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9-

Clave InChI

SPWSUFUPTSJWNG-SXGWCWSVSA-N

Categorías relacionadas

Aplicación

Roquefortine C has been used as a standard for the quantification of roquefortine C by high-performance liquid chromatography (HPLC). It has also been used as a standard for the quantification of roquefortine C by liquid chromatography-mass spectrometry (LC−MS/MS).

Acciones bioquímicas o fisiológicas

Roquefortine C is a paralytic neurotoxin of a dioxopiperazine structure produced by a diverse range of fungi, most notably Penicillium species.
Roquefortine C is a paralytic neurotoxin of a dioxopiperazine structure produced by a diverse range of fungi, most notably Penicillium species. It has been found in blue cheese and in many other food products due to natural occurrence and contamination. Roquefortine C was found to be active on a wide range of organisms. It inhibits the growth of Gram-positive bacteria, and cockerels treated with roquefortine lost their righting reflex and died within 8-12 hours. Mice injected with roquefortine C experienced neurotoxic properties. Roquefortine C was also reported to inhibit cytochrome P450 as well as tubulin polymerization.

Nota de preparación

Soluble in methanol (10 mg/mL), DMSO (10 mg/mL), ethyl acetate (1 mg/mL) and chloroform (1 mg/mL). DMSO solution at 10 mg/mL is stable for 3 months at −20 °C.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Ramón O García-Rico et al.
Microbiology (Reading, England), 154(Pt 11), 3567-3578 (2008-10-30)
We have studied the role of the pga1 gene of Penicillium chrysogenum, encoding the alpha subunit of a heterotrimeric G protein, in secondary metabolite production. The dominant activating pga1(G42R) mutation caused an increase in the production of the three secondary
T W Naudé et al.
Journal of the South African Veterinary Association, 73(4), 211-215 (2003-04-01)
Two dogs developed alarming tremorgenic nervous stimulation shortly after ingesting discarded rice that had been forgotten in a refrigerator for an undetermined period and that was covered with a grey-green mould. Both dogs exhibited vomition followed by slight salivation, tremors
A natural short pathway synthesizes roquefortine C but not meleagrin in three different Penicillium roqueforti strains
Kosalkova K, et al.
Applied Microbiology and Biotechnology, 99(18), 7601-7612 (2015)
Katarina Kosalková et al.
Biochimie, 91(2), 214-225 (2008-10-28)
The biosynthesis of the beta-lactam antibiotic penicillin is an excellent model for the study of secondary metabolites produced by filamentous fungi due to the good background knowledge on the biochemistry and molecular genetics of the beta-lactam producing microorganisms. The three
Ben Clark et al.
Journal of natural products, 68(11), 1661-1664 (2005-11-29)
The new isoprenylated diketopiperazine roquefortine E (6) has been isolated from an Australian soil isolate of the ascomycete Gymnoascus reessii. The known fungal metabolite roquefortine C (1) was also recovered as the major antibacterial principle, and all structures were assigned

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